Asymmetric Total Synthesis of (−)-Erogorgiaene and Its C-11 Epimer and Investigation of Their Antimycobacterial Activity

A short, nine-step, highly enantioselective synthesis of (−)-erogorgiaene and its C-11 epimer is reported. The key stereochemistry controlling steps involve catalytic asymmetric crotylation, anionic oxy-Cope rearrangement and cationic cyclisation. (−)-Erogorgiaene exhibited promising antitubercular activity against multidrug-resistant strains of Mycobacterium tuberculosis. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Авторы
Incerti-Pradillos C.A. 1 , Kabeshov M.A. 1 , O'hora P.S. 1 , Shipilovskikh S.A. 2, 1 , Rubtsov A.E. 2 , Drobkova V.A. 2 , Balandina S.Y. 2 , Malkov A.V. 1, 3
Журнал
Chemistry - A European Journal
Издательство
Wiley-VCH Verlag
Номер выпуска
40
Язык
Английский
Страницы
14390-14396
Статус
Опубликовано
Ссылка
Внешняя ссылка
DOI
10.1002/CHEM.201602440
Том
22
Год
2016
Организации
  • 1 Department of Chemistry, Loughborough University, Loughborough, LE11 3TU, United Kingdom
  • 2 Department of Chemistry, Perm State University, Bukireva 15, Perm, 614990, Russian Federation
  • 3 Chemistry Department, Peoples' Friendship University of Russia, Miklukho-Maklaya 6, Moscow, 117198, Russian Federation
Ключевые слова
allylation; asymmetric catalysis; enantioselectivity; rearrangement; total synthesis
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